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The Pros of Being a Pessimist

By Megan Collins | Last Updated: Oct 14 2016


There’s plenty of evidence pointing to the power of positive thinking (even here!), but what about the power of negative thinking? When it comes to shopping, at least, thinking like a pessimist will guarantee you end up with a closet of clothes you don’t regret. Of course, I don’t want you walking around the mall with a rain cloud over your head like Eeyore, but it is helpful to look at your wardrobe with a more critical eye. Below, a few tips on taking a “closet half empty” approach to your clothes:

Be cynical.

We often say about a love gone wrong, “I always felt like there was something off about him/her; I wish I’d listened to my gut.” When you’re shopping, pay attention to the little voice inside that says, “This isn’t your color!” or “Even Tim Gunn couldn’t fix the shoulders in this suit!” It’s especially tempting to shout this voice down at the clearance rack. You think, “I would totally wear this double-breasted seersucker suit if I’m ever invited to the Kentucky Derby!” Listen to the voice in your head – if it’s telling you the item in your hands will die a slow death in the back of your closet, it probably will.

Be ruthless.

Pessimists are quick to point out the negative. The flaw in a well-laid plan, the fly in the soup. When you look in your closet, take a “Guilty till proven innocent” attitude towards its contents. Is there a pair of pleated pants that haven’t seen daylight since 1992? Get rid of them. A neon green sweater you never could figure out what to wear it with? Donate it. A good rule of thumb: if you haven’t worn it in two seasons (the shorts that didn’t get any wear this summer or last, for instance), give it the ol’ heave-ho.

Be skeptical.

When it comes to cost, it pays to be skeptical. Consider the longevity of the item you’re buying. If it’s part of a trend that will be “out” at the end of the season, pick it up on the cheap. If, on the other hand, it’s an investment piece you’ll have forever (like sturdy dress shoes or a warm overcoat), spend what you can afford.

Be bitter.

Do you ever stand in front of your closet complaining that, even though it’s stuffed to the brim, you haven’t got anything to wear? You deserve better than a closet full of ill-fitting, ugly clothes. Don’t take it anymore! If you’re mad enough about being burned by poor clothing purchases in the past, you won’t let it happen in the future. Like The Who promised, we won’t be fooled again.